(3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one | 172806-92-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one
• 英文别名: (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydroisochromen-1-one
• CAS: 172806-92-7
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: UWSQDVQKLXZPMB-HCVRKRLWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one 、 甲氧基-三氟甲基苯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以90%的产率得到
  参考文献：
  名称：

  Synthesis of an insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one

  摘要：

  The insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one, was synthesized as a racemate and as an optically active form using one-potesterification-Michael addition-aldol reaction of delta-hydroxy-alpha,beta-unsaturated aldehyde and diketene as a key step. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.006
• 作为产物：
  描述：

  (3R,4S,4aR)-8-hydroxy-4-methoxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one 在 三溴化硼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.5h， 以77%的产率得到(3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one
  参考文献：
  名称：

  Synthesis of an insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one

  摘要：

  The insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one, was synthesized as a racemate and as an optically active form using one-potesterification-Michael addition-aldol reaction of delta-hydroxy-alpha,beta-unsaturated aldehyde and diketene as a key step. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.006

文献信息

• Synthesis of an insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one
  作者：Kanako Uchida、Ken Ishigami、Hidenori Watanabe、Takeshi Kitahara

  DOI：10.1016/j.tet.2006.11.006

  日期：2007.1

  The insecticidal tetrahydroisocoumarin, (3R,4S,4aR)-4,8-dihydroxy-3-methyl-3,4,4a,5-tetrahydro-1H-2-benzopyran-1-one, was synthesized as a racemate and as an optically active form using one-potesterification-Michael addition-aldol reaction of delta-hydroxy-alpha,beta-unsaturated aldehyde and diketene as a key step. (c) 2006 Elsevier Ltd. All rights reserved.